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During his much-heralded three-day visit to Jordan, the West Bank, and Israel, starting Friday, Pope Francis will have the opportunity to cement his personally warm relations with members of the Jewish community, a group with which the Vatican is still repairing the damage from centuries of troubled dealings.

Francis, the first pope to walk on Israeli soil since John Paul II 14 years ago, is scheduled to meet Monday in Jerusalem with the Jewish state’s two chief rabbis, pay homage at the Yad Vashem Holocaust Memorial, visit the grave of Zionism founder Theodor Herzl, and confer with Israeli Prime Minister Benjamin Netanyahu and President Shimon Peres.

But in a little-noticed aspect of the papal schedule, Francis also is planning to meet with Jerusalem’s grand mufti, Sheikh Muhammad Hussein, an Islamic cleric with a history of outspoken anti-Semitism, of praising suicide bombers, and of exhorting Muslims to kill Jews.

In a January 2012 sermon in the Arab quarter of East Jerusalem, the sheikh quoted approvingly from “the reliable Hadith,” the traditionally accepted account of the sayings of the Prophet Muhammad:

“‘The Hour [of Resurrection] will not come until you fight the Jews. / The Jew will hide behind stones or trees. / Then the stones or trees will call: ‘Oh Muslim, servant of Allah, there is a Jew behind me, come and kill him.’”

Predictably, Netanyahu called the sheikh’s sermon “a very serious offense that all the countries of the world must condemn,” and the European Union and the British government rebuked the cleric. At the same event, another speaker reportedly referred to Jews as “descendants of monkeys and pigs.”

In other public forums, Sheikh Hussein has claimed that Jews are “enemies of Allah” and that suicide bombers are “an elite group of martyrs.”

Surely the granting of a papal audience to such a spewer of inflammatory Jew-hatred has the potential to rip the scab off historically raw wounds. It also places Francis’s Israeli hosts in an awkward spot. Netanyahu has called for the sheikh’s prosecution and demanded, to no avail, that Palestinian Authority President Mahmoud Abbas also condemn him.

Thus the pope, who has insisted that his sojourn in the Holy Land is “purely a religious” visit, will confront a delicate dilemma. Should he simply snub the grand mufti? To expect the pope to show disrespect publicly to the leading Muslim cleric in the Palestinian Authority, and by extension his thousands of followers, seems unrealistic and ultimately short-sighted. The more productive and courageous course would be for Francis to meet with the sheikh and offer criticism of Hussein’s pattern of ugly rhetoric.

So far leaders in the Jewish community have appeared reluctant to complain about Francis’s meeting with the sheikh and willing to give the pope some running room. Rabbi David Rosen, director of international interreligious affairs for the American Jewish Committee, told The Daily Beast: “It’s not for me to raise objections. I can’t see how the pope can come here and not meet with Muslim officials.”

Likewise, Menachem Rosensaft, general counsel of the World Jewish Congress and a lecturer at Columbia Law School, said: “I would expect him to use his office and his moral influence to promote the peace process by any means he deems appropriate.” Rosensaft, the son of Holocaust survivors, added: “I am not going to second-guess from afar who he meets with.”

Showing a deft touch for human relations and for making friends and influencing people, the pope sent a personal email to the professor last October, an expression of good will that Rosensaft said he treasures.

The history of the relationship between the Vatican and world Jewry is a different story. It wasn’t until the Second Vatican Council of 1965,under Pope Paul VI, that the Roman Catholic Church absolved the Jewish people of collective guilt for the crucifixion of Jesus. And it was only in 1994, under John Paul II, that the Vatican gave diplomatic recognition to the state of Israel. In his 2000 visit to Israel, the Polish pope placed a note at the Wailing Wall seeking forgiveness for Christian anti-Semitism.

Philip Cunningham, director of the Institute for Jewish-Catholic Relations of St. Joseph's University, told The Daily Beast that Pope Francis’s visit to Israel continues the trajectory of Jewish-Catholic rapprochement, which was accelerated under John Paul II and Pope Benedict XVI.

But Cunningham said Francis is different from his two immediate predecessors in that he has forged close friendships with Jewish leaders, as he did with Argentine Rabbi Abraham Skorka when the pope was Cardinal Jorge Mario Bergoglio, the archbishop of Buenos Aires. “His relationship with the Jewish community,” Cunningham said, “is immediate and personal.” Skorka will accompany Francis to the Middle East, along with Sheik Omar Abboud, also from the pope’s native Argentina. It is the first time a papal delegation has included clerics of other faiths.

“I think Francis believes that you don’t accomplish anything by refusing to talk with people,” Cunningham said. “He is aware that the conflicts of the Middle East are not going to be resolved absent dialogue with all religious leaders. You can’t start a conversation by saying all the things that you dislike about someone.”

Yet getting up close and personal with the mufti will require every bit of Francis’s unifying energy.

When tensions have erupted in recent years, as they did over the effort by Carmelite nuns to open a convent near the site of the Auschwitz death camp, the conflict has been historical in nature. Denouncing historical anti-Semitism in the abstract is easy enough for popes, especially when they have avoided facing up to the Catholic Church’s historical complicity.

But when he shakes hands with the sheikh on Monday, he will meet a man who embodies the most lethal form of Jew-hatred in the world today. It remains to be seen whether the pope will confront Hussein directly, fudge the matter with platitudes about the evils of anti-Semitism, or simply ignore the mufti’s hateful record and hope that Jews will just turn the other cheek about his calls for their extermination.